Document Report Card

ID: ALA1125694

Journal: J Med Chem

Title: Fluorinated sugar analogues of potential anti-HIV-1 nucleosides.

Authors: Huang JT, Chen LC, Wang LB, Kim MH, Warshaw JA, Armstrong D, Zhu QY, Chou TC, Watanabe KA, Matulic-Adamic J.

Abstract: In order to obtain agents with therapeutic indices superior to those of AZT, FLT, or D4T, several analogues of anti-HIV-1 nucleosides were synthesized. These include 2',3'-dideoxy-2',3' -difluoro-5-methyluridine (13), its arabino analogue 19, arabino-5-methylcytosine analogue 21, 3'-deoxy-2',3'-didehydro-2' -fluorothymidine (25), 3'-azido-2',3'-dideoxy-2'-fluoro-5-methyluridine (29), 2'-azido-3'-fluoro-2',3'-dideoxy-5-methyluridine (31), and 2'3'-dideoxy-2' -fluoro-5-methyluridine (37). These new nucleosides were screened for their activity against HIV and feline TLV in vitro. None of the compounds showed significant activity. It is interesting to note that such a small modification in the sugar moiety of active anti-HIV nucleosides (i.e., displacement of hydrogen by fluorine) almost completely inactivate the agents.

CiteXplore: 2033590

DOI: 10.1021/jm00109a017